Where do people shop in Carlisle? I only saw one grocery store! Where do people do anything there?http://www.visitccpa.com/
There is the Carlisle Mall, but it isn't that big and Harrisburg has 2-3 more. If you want a lot of shopping, there are a ton of outlet malls in Hershey and Lancaster. I live in York (about 30min SE) of Carlisle. For high-end shopping there is the King of Prussia Mall near Philly.
Every summer Carlisle hosts a series of events at the fairgrounds. That is usually when I go there. They have a bike show and car show that I attend. As far as anything else, well....it is a small town and Harrisburg isn't much better. I enjoy AAA baseball and Harrisburg has a team that plays on City Island. There is some really nice camping and hunting around there. There are cultural events around here, but you often have to pay attention and look for them. There are enough historical areas if you are into that stuff. Gettysburg is really close and that makes for a nice day trip. Ski Roundtop is pretty close to Carlisle and there is fishing and boating on the Susquehanna. Hersheypark is really close and they have some great rides there as well.
If you are into the bar and club scene and are used to big cities, then this place will most likely be a dissapointment. I used to live near LA and Vegas. I came away very spoiled and have yet to find anything close to that here. If you like the quieter pub atmosphere, you should be fine though. I find that if I want to do anything fun I have to go look for it which is pretty consistent with most small towns I have lived in. It is there, but not screaming at you all the time like in a larger city.